Showing metabocard for Camphene (MMDBc0047673)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:37:10 UTC
Update Date2024-04-30 20:28:33 UTC
Metabolite IDMMDBc0047673
Metabolite Identification
Common NameCamphene
DescriptionCamphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene is nearly insoluble in water but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It exists as a flammable, white solid that has a minty, citrus, eucalyptus odor. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and in food additives for flavouring. In the mid-19th century it was used as a fuel for lamps, but this was limited by its explosiveness. Camphene exists in all eukaryotes, ranging from yeast to plants to humans. Camphene can be found in a number of food items such as dill, carrots, caraway, hyssop, lemon, orange, nutmeg seed, parsley, sage, thyme, turmeric and fennel, which makes camphene a potential biomarker for the consumption of these food products. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. Camphene is one of several monoterpenes that are found in cannabis plants (PMID:6991645 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46dc3f70a8>

camphene
  Mrv1652305271900052D          

 10 11  0  0  0  0            999 V2000
    0.2522   -2.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764   -1.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f46dc3f70a8>

HMDB0059839
     RDKit          3D
Camphene
 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.3016    1.4991    1.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    0.5043    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2873   -0.2134    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1282    0.4573   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926    0.2775   -1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.7448   -1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378   -1.4962    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8757   -0.0881   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -1.1037    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    0.9380   -0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262    1.8400    2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2781    1.9745    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7797   -0.3906    1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -0.0942   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2637    1.5064    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7178    1.2605   -1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762    0.0070   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -1.3790   -1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -1.9867   -0.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -2.1475    0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8358   -2.0598   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557   -1.3580    1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -0.6376    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    1.8851   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8940    0.4971   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684    1.0527   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  8  2  1  0
  7  3  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f46dc3f70a8>

camphene
  Mrv1652305271900052D          

 10 11  0  0  0  0            999 V2000
    0.2522   -2.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764   -1.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047673

> <DATABASE_NAME>
MIME

> <SMILES>
CC1(C)C2CCC(C2)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3

> <INCHI_KEY>
CRPUJAZIXJMDBK-UHFFFAOYSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
16.951074738158884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
2.859595116666666

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
43.6498

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
camphene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f46dc3f70a8>

HMDB0059839
     RDKit          3D
Camphene
 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.3016    1.4991    1.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    0.5043    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2873   -0.2134    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1282    0.4573   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926    0.2775   -1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.7448   -1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378   -1.4962    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8757   -0.0881   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -1.1037    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    0.9380   -0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262    1.8400    2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2781    1.9745    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7797   -0.3906    1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -0.0942   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2637    1.5064    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7178    1.2605   -1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762    0.0070   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -1.3790   -1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -1.9867   -0.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -2.1475    0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8358   -2.0598   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557   -1.3580    1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -0.6376    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    1.8851   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8940    0.4971   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684    1.0527   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  8  2  1  0
  7  3  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
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PDB for #<Metabolite:0x00007f46dc3f70a8>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: camphene                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.471  -5.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.252  -3.846   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.263  -3.568   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.700  -3.117   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.063  -3.808   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.614  -2.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.129  -1.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.831  -0.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.934  -2.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.212  -1.584   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7    2   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for #<Metabolite:0x00007f46dc3f70a8>

COMPND    HMDB0059839
HETATM    1  C1  UNL     1      -0.302   1.499   1.781  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.003   0.504   0.931  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.287  -0.213   0.876  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.128   0.457  -0.194  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.193   0.277  -1.402  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.181  -0.745  -1.010  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.938  -1.496   0.101  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.876  -0.088  -0.121  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.761  -1.104   0.536  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.665   0.938  -0.874  1.00  0.00           C  
HETATM   11  H1  UNL     1       0.426   1.840   2.504  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.278   1.975   1.755  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.780  -0.391   1.803  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.079  -0.094  -0.361  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.264   1.506   0.068  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.718   1.261  -1.555  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.776   0.007  -2.303  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.208  -1.379  -1.773  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.836  -1.987  -0.295  1.00  0.00           H  
HETATM   20  H10 UNL     1       0.279  -2.148   0.675  1.00  0.00           H  
HETATM   21  H11 UNL     1      -1.836  -2.060  -0.031  1.00  0.00           H  
HETATM   22  H12 UNL     1      -1.456  -1.358   1.573  1.00  0.00           H  
HETATM   23  H13 UNL     1      -2.784  -0.638   0.636  1.00  0.00           H  
HETATM   24  H14 UNL     1      -1.155   1.885  -1.039  1.00  0.00           H  
HETATM   25  H15 UNL     1      -1.894   0.497  -1.888  1.00  0.00           H  
HETATM   26  H16 UNL     1      -2.668   1.053  -0.392  1.00  0.00           H  
CONECT    1    2    2   11   12
CONECT    2    3    8
CONECT    3    4    7   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7    8   18
CONECT    7   19   20
CONECT    8    9   10
CONECT    9   21   22   23
CONECT   10   24   25   26
END
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SMILES for #<Metabolite:0x00007f46dc3f70a8>

CC1(C)C2CCC(C2)C1=C
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INCHI for #<Metabolite:0x00007f46dc3f70a8>

InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3
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Synonyms
ValueSource
2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptaneChEBI
2,2-Dimethyl-3-methylenenorbornaneChEBI
3,3-Dimethyl-2-methylenenorbornaneChEBI
3,3-Dimethyl-2-methylenenorcamphaneChEBI
CompheneChEBI
3,3-Dimethyl-2-methylidenebicyclo[2.2.1]heptaneHMDB
Molecular FormulaC10H16
Average Mass136.238
Monoisotopic Mass136.125200515
IUPAC Name2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane
Traditional Namecamphene
CAS Registry NumberNot Available
SMILES
CC1(C)C2CCC(C2)C1=C
InChI Identifier
InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3
InChI KeyCRPUJAZIXJMDBK-UHFFFAOYSA-N